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Hydrazine hydrate (1:1) → 8-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

HRID 1059427
Notes
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Reaction equation

HRID 1059427 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][N:15]3C(=O)C4=CC=CC=C4C3=O)[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:26]=[CH:27][CH:28]=[N:29][C:5]1=2.O.NN>C(O)C>[NH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]2[S:7][C:6]3[N:26]=[CH:27][CH:28]=[N:29][C:5]=3[N:4]([CH2:3][O:2][CH3:1])[C:9]=2[CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18670612N-(10-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)phthalimide

Product 1

HCID 186704238-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazineYield 100.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1.3 g of N-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)phthalimide in 20 ml of ethanol was added 5 ml of hydrazine monohydrate and the resulting mixture was heated to 60° C. for 10 minutes. After distilling off the solvent under reduced pressure, the residue was distributed into a 5% aqueous solution of sodium hydroxide and ethyl acetate. The organic layer was extracted and the extract was dried over potassium carbonate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia) to thereby give 890 mg of the title compound as a yellow oily substance.

Workup

  1. distillationAfter distilling off the solvent under reduced pressure
  2. extractionThe organic layer was extracted
  3. dry with materialthe extract was dried over potassium carbonate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia)

Sources & evidence

ORD record
ord-4bbd95010bb649d5ac95b904b52fb8be
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06518423B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes